Photocontrolled template-directed synthesis of complementary double helices assisted by amidinium–carboxylate salt bridge formation

The template-directed imine-bond forming reactions between chiral amidines or achiral carboxylic acids monomers bearing a formyl or an amino group at one end were remarkably accelerated 34- or 10-fold in chloroform in the presence of the corresponding optically inactive carboxylic acid dimer or opti...

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Bibliographic Details
Published inChemical science (Cambridge) Vol. 4; no. 7; pp. 2960 - 2966
Main Authors Tanabe, Junki, Taura, Daisuke, Yamada, Hidekazu, Furusho, Yoshio, Yashima, Eiji
Format Journal Article
LanguageEnglish
Published 01.01.2013
Subjects
Bearing
Carboxylic acids
Conversion
Dimers
Helices
Monomers
Optical activity
Synthesis
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Summary:The template-directed imine-bond forming reactions between chiral amidines or achiral carboxylic acids monomers bearing a formyl or an amino group at one end were remarkably accelerated 34- or 10-fold in chloroform in the presence of the corresponding optically inactive carboxylic acid dimer or optically active amidine dimer linked by a trans-azobenzene unit as the template, respectively. The cis-azobenzene-linked carboxylic acid template markedly slowed the monomer conversions, and hence a reversible photocontrolled dimerization was achieved by light-induced cis-transisomerization upon alternative irradiation with UV and visible light.
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ISSN:2041-6520
2041-6539
DOI:10.1039/c3sc50833a